Diedre Windsor, a retired US Army Officer, and former member of the federal Senior Executive Service (SES), is the founder and CEO of Windsor Group LLC (Windsor). Windsor is an award-winning professional services company, based in Bethesda, Maryland, that provides services to public and private-sector clients. Windsor serves its clients in the areas of Staff Augmentation, Project and Program Management, IT Support, and Training and Development. Windsor is a certified 8(a), woman and service-disabled veteran-owned small business and holds a GSA Multiple Award Schedules (MAS) contract. Windsor is also the prime vendor in an all-small joint venture, 360 Innovative Solutions, that holds the 8(a) STARS III contract vehicle. 

Founded in 2010 and operational since 2017, Windsor Group LLC achieved No. 191 on the 5000 list of America’s Fastest-Growing Private Companies with 2,225% growth, and No. 17 on the 2022 Vet100. These accolades were repeated for three consecutive years. Windsor also made the lists of Greater Washington’s 50 fastest-growing companies and top corporate philanthropists in 2023 and 2024. Diedre and Windsor Group were ranked #5 on the Women Presidents Organization 2024 list of the 50 Fastest Growing Women-Owned and -Led Companies.

Diedre is dedicated to community service, contributing time and resources to numerous nonprofits, including ROCKS, Inc., RMOA Business Association (RBA), Code of Support Foundation (COSF), Veterans Institute for Procurement (VIP), Military Women’s Memorial, Women Veterans Interactive Foundation, Army Women’s Foundation, Sallie Eaton Benevolence Foundation, Agape Love in Action, and the Institute for Entrepreneurial Leadership.

In 2023, Diedre was named to the Daily Record’s list of Maryland’s Top 100 Women and won the “Enterprising Women of the Year” award by Enterprising Women Magazine. She is a member of C200, the Women Presidents Organization (WPO), The BOW Collective, Women’s Business Enterprise Council Greater DMV, CEO Roundtable, Military Officers Association (MOAA), Alpha Kappa Alpha Sorority, Inc., and serves on the Boards of Code of Support Foundation, Military Women’s Memorial, and RMOA Business Association.

Diedre holds a Bachelor of Science in Political Science from Methodist University and a master’s degree in Human Resource Management from Webster University. In 2015, she authored “Leadership Begins with Hello! Practical Principles of Leadership ~ A Hip-pocket Guide.” She resides in Bethesda with her family.